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fix(email): close SMTP and IMAP connections on failure (#3804)

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SMTP connections in _send_email() and _send_email_with_attachment() leak
when login() or send_message() raises before quit() is reached. Both now
wrapped in try/finally with a close() fallback if quit() also fails.

IMAP connection in _fetch_new_messages() leaks when UID processing raises,
since logout() sits after the loop. Restructured with try/finally so
logout() runs unconditionally.

Co-authored-by: Himess <Himess@users.noreply.github.com>
This commit is contained in:
Teknium
2026-03-29 15:38:32 -07:00
committed by GitHub
parent ee3d2941cc
commit 8eb70a6885
2 changed files with 185 additions and 55 deletions
Download Patch File Download Diff File Expand all files Collapse all files

123
gateway/platforms/email.py
View File

@@ -337,60 +337,63 @@ class EmailAdapter(BasePlatformAdapter):
results = [] results = []
try: try:
imap = imaplib.IMAP4_SSL(self._imap_host, self._imap_port, timeout=30) imap = imaplib.IMAP4_SSL(self._imap_host, self._imap_port, timeout=30)
imap.login(self._address, self._password) try:
imap.select("INBOX") imap.login(self._address, self._password)
imap.select("INBOX")
status, data = imap.uid("search", None, "UNSEEN") status, data = imap.uid("search", None, "UNSEEN")
if status != "OK" or not data or not data[0]: if status != "OK" or not data or not data[0]:
imap.logout() return results
return results
for uid in data[0].split(): for uid in data[0].split():
if uid in self._seen_uids: if uid in self._seen_uids:
continue continue
self._seen_uids.add(uid) self._seen_uids.add(uid)
# Trim periodically to prevent unbounded memory growth # Trim periodically to prevent unbounded memory growth
if len(self._seen_uids) > self._seen_uids_max: if len(self._seen_uids) > self._seen_uids_max:
self._trim_seen_uids() self._trim_seen_uids()
status, msg_data = imap.uid("fetch", uid, "(RFC822)") status, msg_data = imap.uid("fetch", uid, "(RFC822)")
if status != "OK": if status != "OK":
continue continue
raw_email = msg_data[0][1] raw_email = msg_data[0][1]
msg = email_lib.message_from_bytes(raw_email) msg = email_lib.message_from_bytes(raw_email)
sender_raw = msg.get("From", "") sender_raw = msg.get("From", "")
sender_addr = _extract_email_address(sender_raw) sender_addr = _extract_email_address(sender_raw)
sender_name = _decode_header_value(sender_raw) sender_name = _decode_header_value(sender_raw)
# Remove email from name if present # Remove email from name if present
if "<" in sender_name: if "<" in sender_name:
sender_name = sender_name.split("<")[0].strip().strip('"') sender_name = sender_name.split("<")[0].strip().strip('"')
subject = _decode_header_value(msg.get("Subject", "(no subject)")) subject = _decode_header_value(msg.get("Subject", "(no subject)"))
message_id = msg.get("Message-ID", "") message_id = msg.get("Message-ID", "")
in_reply_to = msg.get("In-Reply-To", "") in_reply_to = msg.get("In-Reply-To", "")
# Skip automated/noreply senders before any processing # Skip automated/noreply senders before any processing
msg_headers = dict(msg.items()) msg_headers = dict(msg.items())
if _is_automated_sender(sender_addr, msg_headers): if _is_automated_sender(sender_addr, msg_headers):
logger.debug("[Email] Skipping automated sender: %s", sender_addr) logger.debug("[Email] Skipping automated sender: %s", sender_addr)
continue continue
body = _extract_text_body(msg) body = _extract_text_body(msg)
attachments = _extract_attachments(msg, skip_attachments=self._skip_attachments) attachments = _extract_attachments(msg, skip_attachments=self._skip_attachments)
results.append({ results.append({
"uid": uid, "uid": uid,
"sender_addr": sender_addr, "sender_addr": sender_addr,
"sender_name": sender_name, "sender_name": sender_name,
"subject": subject, "subject": subject,
"message_id": message_id, "message_id": message_id,
"in_reply_to": in_reply_to, "in_reply_to": in_reply_to,
"body": body, "body": body,
"attachments": attachments, "attachments": attachments,
"date": msg.get("Date", ""), "date": msg.get("Date", ""),
}) })
finally:
imap.logout() try:
imap.logout()
except Exception:
pass
except Exception as e: except Exception as e:
logger.error("[Email] IMAP fetch error: %s", e) logger.error("[Email] IMAP fetch error: %s", e)
return results return results
@@ -503,10 +506,15 @@ class EmailAdapter(BasePlatformAdapter):
msg.attach(MIMEText(body, "plain", "utf-8")) msg.attach(MIMEText(body, "plain", "utf-8"))
smtp = smtplib.SMTP(self._smtp_host, self._smtp_port, timeout=30) smtp = smtplib.SMTP(self._smtp_host, self._smtp_port, timeout=30)
smtp.starttls(context=ssl.create_default_context()) try:
smtp.login(self._address, self._password) smtp.starttls(context=ssl.create_default_context())
smtp.send_message(msg) smtp.login(self._address, self._password)
smtp.quit() smtp.send_message(msg)
finally:
try:
smtp.quit()
except Exception:
smtp.close()
logger.info("[Email] Sent reply to %s (subject: %s)", to_addr, subject) logger.info("[Email] Sent reply to %s (subject: %s)", to_addr, subject)
return msg_id return msg_id
@@ -590,10 +598,15 @@ class EmailAdapter(BasePlatformAdapter):
msg.attach(part) msg.attach(part)
smtp = smtplib.SMTP(self._smtp_host, self._smtp_port, timeout=30) smtp = smtplib.SMTP(self._smtp_host, self._smtp_port, timeout=30)
smtp.starttls(context=ssl.create_default_context()) try:
smtp.login(self._address, self._password) smtp.starttls(context=ssl.create_default_context())
smtp.send_message(msg) smtp.login(self._address, self._password)
smtp.quit() smtp.send_message(msg)
finally:
try:
smtp.quit()
except Exception:
smtp.close()
return msg_id return msg_id

117
tests/gateway/test_email.py
View File

@@ -1057,5 +1057,122 @@ class TestSendEmailStandalone(unittest.TestCase):
self.assertIn("not configured", result["error"]) self.assertIn("not configured", result["error"])
class TestSmtpConnectionCleanup(unittest.TestCase):
"""Verify SMTP connections are closed even when send_message raises."""
@patch.dict(os.environ, {
"EMAIL_ADDRESS": "hermes@test.com",
"EMAIL_PASSWORD": "secret",
"EMAIL_IMAP_HOST": "imap.test.com",
"EMAIL_SMTP_HOST": "smtp.test.com",
"EMAIL_SMTP_PORT": "587",
}, clear=False)
def _make_adapter(self):
from gateway.config import PlatformConfig
from gateway.platforms.email import EmailAdapter
return EmailAdapter(PlatformConfig(enabled=True))
@patch.dict(os.environ, {
"EMAIL_ADDRESS": "hermes@test.com",
"EMAIL_PASSWORD": "secret",
"EMAIL_IMAP_HOST": "imap.test.com",
"EMAIL_SMTP_HOST": "smtp.test.com",
"EMAIL_SMTP_PORT": "587",
}, clear=False)
def test_smtp_quit_called_on_send_message_failure(self):
"""SMTP quit() must be called even when send_message() raises."""
adapter = self._make_adapter()
mock_smtp = MagicMock()
mock_smtp.send_message.side_effect = Exception("send failed")
with patch("smtplib.SMTP", return_value=mock_smtp):
with self.assertRaises(Exception):
adapter._send_email("user@test.com", "Hello")
mock_smtp.quit.assert_called_once()
@patch.dict(os.environ, {
"EMAIL_ADDRESS": "hermes@test.com",
"EMAIL_PASSWORD": "secret",
"EMAIL_IMAP_HOST": "imap.test.com",
"EMAIL_SMTP_HOST": "smtp.test.com",
"EMAIL_SMTP_PORT": "587",
}, clear=False)
def test_smtp_close_called_when_quit_also_fails(self):
"""If both send_message() and quit() fail, close() is the fallback."""
adapter = self._make_adapter()
mock_smtp = MagicMock()
mock_smtp.send_message.side_effect = Exception("send failed")
mock_smtp.quit.side_effect = Exception("quit failed")
with patch("smtplib.SMTP", return_value=mock_smtp):
with self.assertRaises(Exception):
adapter._send_email("user@test.com", "Hello")
mock_smtp.close.assert_called_once()
class TestImapConnectionCleanup(unittest.TestCase):
"""Verify IMAP connections are closed even when fetch raises."""
@patch.dict(os.environ, {
"EMAIL_ADDRESS": "hermes@test.com",
"EMAIL_PASSWORD": "secret",
"EMAIL_IMAP_HOST": "imap.test.com",
"EMAIL_IMAP_PORT": "993",
"EMAIL_SMTP_HOST": "smtp.test.com",
}, clear=False)
def _make_adapter(self):
from gateway.config import PlatformConfig
from gateway.platforms.email import EmailAdapter
return EmailAdapter(PlatformConfig(enabled=True))
@patch.dict(os.environ, {
"EMAIL_ADDRESS": "hermes@test.com",
"EMAIL_PASSWORD": "secret",
"EMAIL_IMAP_HOST": "imap.test.com",
"EMAIL_IMAP_PORT": "993",
"EMAIL_SMTP_HOST": "smtp.test.com",
}, clear=False)
def test_imap_logout_called_on_uid_fetch_failure(self):
"""IMAP logout() must be called even when uid fetch raises."""
adapter = self._make_adapter()
mock_imap = MagicMock()
def uid_handler(command, *args):
if command == "search":
return ("OK", [b"1"])
if command == "fetch":
raise Exception("fetch failed")
return ("NO", [])
mock_imap.uid.side_effect = uid_handler
with patch("imaplib.IMAP4_SSL", return_value=mock_imap):
results = adapter._fetch_new_messages()
self.assertEqual(results, [])
mock_imap.logout.assert_called_once()
@patch.dict(os.environ, {
"EMAIL_ADDRESS": "hermes@test.com",
"EMAIL_PASSWORD": "secret",
"EMAIL_IMAP_HOST": "imap.test.com",
"EMAIL_IMAP_PORT": "993",
"EMAIL_SMTP_HOST": "smtp.test.com",
}, clear=False)
def test_imap_logout_called_on_early_return(self):
"""IMAP logout() must be called even when returning early (no unseen)."""
adapter = self._make_adapter()
mock_imap = MagicMock()
mock_imap.uid.return_value = ("OK", [b""])
with patch("imaplib.IMAP4_SSL", return_value=mock_imap):
results = adapter._fetch_new_messages()
self.assertEqual(results, [])
mock_imap.logout.assert_called_once()
if __name__ == "__main__": if __name__ == "__main__":
unittest.main() unittest.main()